Vacation starts before you leave

Leaving the office for vacation: the professional equivalent of the Home Alone scenes when the McCalisters wake up late and rush through the airport.

Taking time off is vital to the health of your company, right? So why does leaving for vacation feel so stressful?

People-first leaders can do better for their teams. Let’s discuss how to create an environment that is mellow and relaxed as our teams go on vacation—whether for a week or just the weekend.

Here's the TL;DR:

• Discuss vacation frequently with your team—starting with 1:1s
• Planning for coverage is important—but don’t overdo it
• Try setting a goal: the day before vacation is a freebie!

Alright, let’s talk about enjoying vacation.

De-stressing departure

The good news is that people-first managers are able to uniquely solve this pre-vacation stress.

For this post, our “vacation Big Hairy Audacious Goal (BHAG)” is to completely clear our team members’ plates the day before vacation.

Here’s why this is important: realistically, folks book trips to maximize their vacation time off—this means booking flights from JFK to Frankfurt on Friday night. I know from experience that I’m worrying about a zillion things on that Friday; I am not doing my best work the day before heading out on holiday.

Discuss vacation frequently

Start with 1:1s

The first place to de-stress your team’s vacation prep is in 1:1s.

Elevate the importance of vacation with a prompt to the weekly agenda—something like, “What upcoming time off do you have planned in the next 4-8 weeks?”.

Discussing time off provides an additional benefit: we can encourage people to actually take time off. Did you know that one study showed 30% of vacation time went unused?!

Put it on the calendar

Of course, you should encourage your team to block off their OOO on the calendar and decline meetings, so that others can gain insights into who’s out when (and can plan accordingly).

Here’s another suggestion: a company-wide shared vacation calendar.

A shared calendar allows team members to add their OOO in a place everyone can see. We can minimize the overhead for managing this calendar by inviting the calendar to your holiday block (for example, add vacations@acme.co as an attendee). This way team members can share as much, or as little, detail as they’re comfortable with.

😉 Remember our BHAG? I’d go so far as to encourage my team to block off the day before they leave—so they can focus on wrapping things up without any distracting meetings.

Tell your team

For smaller teams, the place to discuss availability may be in a team-wide meeting. Managers can include a “Team OOO” section in their weekly meeting notes to give everyone an idea of what’s coming up.

Keep in mind that it’s not necessary to broadcast plans to everyone. Teammates may prefer smaller, functional groups to discuss coverage and how the work will continue to get done.

The place to check in on how coverage is coming along is in 1:1s, e.g., “How can I help you prepare coverage for your trip to Germany so that you have an easy day before your leave?”

Coverage while you’re away

Coverage docs are about business continuity, yes—but also peace of mind. When there's clarity on what needs to be covered (and who's doing what), time off is less stressful for the entire organization.

One way to think about how to prepare for coverage is using a known-known matrix.

Ask your team members to provide a breakdown in your 1:1s for your review!

Known-knowns: these are items that already exist on a calendar, task list, and/or project management software. Team members can prepare these things in advance (so coverage might not be needed) or can easily ask others to cover them:

• Meetings: Ask team members to provide their list of standing meetings and their role in those meetings. What deliverables are needed to prepare in advance? Does someone else have to attend while they’re out? If they run the meeting, who do they suggest take over the agenda? And, thinking really radically, which meetings do they believe could be canceled entirely with minimal impact?
• Deadlines: Are there any deadlines that fall during OOO? What is needed to prepare in advance to hit these deadlines? Could the schedule be adjusted to provide more time until their return?

Known-unknowns: Don’t worry about it—there’s little point in worrying about things we can’t solve today. Go enjoy your vacation!

Unknowns-knowns: These are the things over the past few weeks or months that jumped up suddenly. Ask team members to write a brief sentence about what happened, what they did, and who will be responsible if it happens while they’re away.

• Examples include: Customer support tickets with specific questions from customers, sales needing to make adjustments to contracts based on client requests, or bug fixes by engineers.
• Bonus! This documentation creates a living space that provides the entire organization with a rubric for how to prepare in the future. It helps great managers become even greater.

Unknown-unknowns: again, don’t worry about it! You cannot possibly know these things—go enjoy your vacation!

Counterpoint: Keep it simple

Preparing vacation coverage should reduce stress, but sometimes, it turns into a (stressful) project itself! If you see this happen to your team, it’s your job to help:

• Set expectations for what you’d like to see in a coverage doc. A simple template can help.
• Be clear about what vacation periods require thoughtful coverage planning (and which don’t). Sure, longer breaks need planning (and a coverage plan), but stressing over a long weekend? That's a bit much—it’s not like we “prepare” for emergencies or a random sick day here and there, anyways.

Remember how we use 1:1s to discuss upcoming vacations? This is a wonderful opportunity to suggest how much, or how little, your team members should feel the need to prepare coverage.

Vacation shouldn’t be a burden

When we destress our teams’ holidays, we demonstrate that we put people first.

A proactive approach allows our team members to leave with a clear mind, knowing they’re supported. Tools and techniques like 1:1s, shared calendars, and team meetings allow us to plan ahead for absences and ensure everything runs smoothly.

Now—go enjoy what's left of summer.😎

Tom Buchok is a hands-on management coach who focuses on people-first principles. Learn more at buchok.com.